4-nitrophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-1-thio-beta-D-glucopyranoside → 4-aminophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-1-thio-beta-D-glucopyranoside

HRID 1903051노트

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HRID 1903051 반응식
[C:1]([O:4][C@@H:5]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:19]([O:25][C@H:26]2[O:43][C@H:42]([CH2:44][O:45][C:46](=[O:48])[CH3:47])[C@@H:37]([O:38][C:39](=[O:41])[CH3:40])[C@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@H:27]2[O:28][C:29](=[O:31])[CH3:30])[C@@H:18]([CH2:49][O:50][C:51](=[O:53])[CH3:52])[O:17][C@H:6]1[S:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)(=[O:3])[CH3:2]>C(O)(=O)C.[Pd]>[C:1]([O:4][C@@H:5]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:19]([O:25][C@H:26]2[O:43][C@H:42]([CH2:44][O:45][C:46](=[O:48])[CH3:47])[C@@H:37]([O:38][C:39](=[O:41])[CH3:40])[C@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@H:27]2[O:28][C:29](=[O:31])[CH3:30])[C@@H:18]([CH2:49][O:50][C:51](=[O:53])[CH3:52])[O:17][C@H:6]1[S:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)(=[O:3])[CH3:2]

참가 물질

4

반응물 1

HCID 542952114-nitrophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-1-thio-beta-D-glucopyranoside

생성물 1

HCID 132789934-aminophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-1-thio-beta-D-glucopyranoside수율 79.3%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid용매

실험 절차

To 91.3 g of 4-nitrophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside suspended in 100 ml of acetic acid was added 10 g of 10% palladium-on-charcoal catalyst in a Parr hydrogenation bottle, and this was hydrogenated on a Parr hydrogenator for 12 hours. The catalyst was filtered from the solution through diatomaceous earth and washed thoroughly with methanol. The solvents were evaporated in vacuo. The residue was dissolved into one liter of toluene and again evaporated. The residue was dissolved in methylene chloride and passed through a pad of magnesium silicate and the volume of the solution was adjusted to about 300 ml. To this was added 1.5 liters of ether and 5 g of activated charcoal, the solution was boiled for 3 minutes, the charcoal was filtered off and the solvents were again evaporated. The yellow foam was crystallized from 1.5 liters of ether to yield 69.6 g of the desired compound as light yellow crystals, isolated in three crops, m.p. 145°-148° C.

후처리

  1. filtrationThe catalyst was filtered from the solution through diatomaceous earth
  2. washwashed thoroughly with methanol
  3. customThe solvents were evaporated in vacuo
  4. dissolutionThe residue was dissolved into one liter of toluene
  5. customagain evaporated
  6. dissolutionThe residue was dissolved in methylene chloride
  7. additionTo this was added 1.5 liters of ether and 5 g of activated charcoal
  8. waitthe solution was boiled for 3 minutes
  9. filtrationthe charcoal was filtered off
  10. customthe solvents were again evaporated
  11. customThe yellow foam was crystallized from 1.5 liters of ether

출처 및 근거

ORD 기록
ord-0905c7fd08cf464888fa2798cefc13fe
출처 데이터셋
uspto-grants-1984_03
특허 번호
US04435387

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